NP-MRD: Showing NP-Card for Serrulatoside (NP0057562)

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Record Information

Version

2.0

Created at

2022-04-28 02:58:48 UTC

Updated at

2022-04-28 02:58:48 UTC

NP-MRD ID

NP0057562

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Serrulatoside

Description

(1R,4aR,7aR)-4-({[(2S,3R,4R,6R)-3,4-dihydroxy-6-({[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Serrulatoside is found in Penstemon serrulatus. Based on a literature review very few articles have been published on (1R,4aR,7aR)-4-({[(2S,3R,4R,6R)-3,4-dihydroxy-6-({[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204582D          

 41 44  0  0  1  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282204582D          

 41 44  0  0  1  0            999 V2000
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    4.2868    5.7750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875   -1.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  6  0  0  0
 21 24  1  1  0  0  0
 20 25  1  6  0  0  0
 19 26  1  6  0  0  0
 26 27  1  0  0  0  0
 11 28  1  6  0  0  0
 10 29  1  6  0  0  0
  3 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
  2 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  1 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057562

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)O[C@H]1OC=C(CO[C@H]2O[C@@H](CO[C@H]3O[C@H](CO)[C@H](O)[C@@H](O)[C@@H]3O)C[C@@H](O)[C@H]2O)[C@@H]2CC=C(CO)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O14/c1-12(2)5-19(31)41-25-20-13(7-28)3-4-16(20)14(9-36-25)10-37-26-21(32)17(30)6-15(39-26)11-38-27-24(35)23(34)22(33)18(8-29)40-27/h3,9,12,15-18,20-30,32-35H,4-8,10-11H2,1-2H3/t15-,16+,17-,18-,20+,21-,22+,23-,24+,25-,26+,27+/m1/s1

> <INCHI_KEY>
QHFLEHBNWPQUDX-AYKQLUFOSA-N

> <FORMULA>
C27H42O14

> <MOLECULAR_WEIGHT>
590.619

> <EXACT_MASS>
590.257456032

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
59.77049092360628

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4aR,7aR)-4-({[(2S,3R,4R,6R)-3,4-dihydroxy-6-({[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate

> <ALOGPS_LOGP>
-0.85

> <JCHEM_LOGP>
-2.273714396333334

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.571781101365648

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.010454159254008

> <JCHEM_PKA_STRONGEST_BASIC>
-2.735419725049928

> <JCHEM_POLAR_SURFACE_AREA>
214.05999999999997

> <JCHEM_REFRACTIVITY>
138.03919999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.87e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aR,7aR)-4-({[(2S,3R,4R,6R)-3,4-dihydroxy-6-({[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  10.780   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  13.090   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002  13.860   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.002   9.240   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.669  10.780   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.669  13.860   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.002  15.400   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336  16.170   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.000   9.240   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.000   6.160   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.465   2.016   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.941  -1.941   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.910  -3.085   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2    6   35                                                  
CONECT    2    1    3   32                                                  
CONECT    3    2    4   30                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   29                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   17   23                                                  
CONECT   23   22                                                            
CONECT   24   21                                                            
CONECT   25   20                                                            
CONECT   26   19   27                                                       
CONECT   27   26                                                            
CONECT   28   11                                                            
CONECT   29   10                                                            
CONECT   30    3   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31    2   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35    1   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Value	Source
(1R,4AR,7ar)-4-({[(2S,3R,4R,6R)-3,4-dihydroxy-6-({[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4ah,5H,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₇H₄₂O₁₄

Average Mass

590.6190 Da

Monoisotopic Mass

590.25746 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)O[C@H]1OC=C(CO[C@H]2O[C@@H](CO[C@H]3O[C@H](CO)[C@H](O)[C@@H](O)[C@@H]3O)C[C@@H](O)[C@H]2O)[C@@H]2CC=C(CO)[C@H]12

InChI Identifier

InChI=1S/C27H42O14/c1-12(2)5-19(31)41-25-20-13(7-28)3-4-16(20)14(9-36-25)10-37-26-21(32)17(30)6-15(39-26)11-38-27-24(35)23(34)22(33)18(8-29)40-27/h3,9,12,15-18,20-30,32-35H,4-8,10-11H2,1-2H3/t15-,16+,17-,18-,20+,21-,22+,23-,24+,25-,26+,27+/m1/s1

InChI Key

QHFLEHBNWPQUDX-AYKQLUFOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penstemon serrulatus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
O-glycosyl compound
Iridoid-skeleton
Glycosyl compound
Monoterpenoid
Bicyclic monoterpenoid
Fatty acid ester
Fatty acyl
Oxane
Monosaccharide
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.85	ALOGPS
logP	-2.3	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.01	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	214.06 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	138.04 m³·mol⁻¹	ChemAxon
Polarizability	59.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163105651

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Serrulatoside (NP0057562)

MOL for NP0057562 (Serrulatoside)

3D MOL for NP0057562 (Serrulatoside)

3D SDF for NP0057562 (Serrulatoside)

3D-SDF for NP0057562 (Serrulatoside)

PDB for NP0057562 (Serrulatoside)

3D PDB for NP0057562 (Serrulatoside)

SMILES for NP0057562 (Serrulatoside)

INCHI for NP0057562 (Serrulatoside)

Structure for NP0057562 (Serrulatoside)

3D Structure for NP0057562 (Serrulatoside)